Reaction #6019

ord-91ea50635080455580c7511d82a79a21

Reaction equation

O=C(O)c1ccc(CBr)cc1
4-(bromomethyl)benzoic acid
CCCCCC
hexane
C[Si](C)(C)C=[N+]=[N-]
trimethylsilyldiazo- methane
N#N
N2
C[Si](C)(C)C=[N+]=[N-]
trimethylsilyldiazomethane
→
COC(=O)c1ccc(CBr)cc1
Methyl 4-(bromomethyl)benzoate

Reactants

O=C(O)c1ccc(CBr)cc1
4-(bromomethyl)benzoic acid
CCCCCC
hexane
C[Si](C)(C)C=[N+]=[N-]
trimethylsilyldiazo- methane
N#N
N2
—
ester
C[Si](C)(C)C=[N+]=[N-]
trimethylsilyldiazomethane

Reagents

None

Solvents

CO
methanol
CCOC(C)=O
ethyl acetate
Cc1ccccc1
toluene

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.STIRRINGLet stir at room temperature for 1 hr

Procedure

To a solution of 1.0 eq of 4-(bromomethyl)benzoic acid in 20 ml of methanol and 50 ml of toluene; was added dropwise 2.05 eq of trimethylsilyldiazomethane while stirring at room temperature. The reaction was titrated until a persistant pale yellow color existed from the addition of excess trimethylsilyldiazo- methane. Let stir at room temperature for 1 hr to insure the complete evolution of N2. Thin layer chromatography in 1:1 hexane:ethyl acetate indicated the disappearance of starting material and the appearance of desired ester with an Rf of 0.7.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05246944uspto-grants-1993_09